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Where’s Homeless Guy? You know, the guy in the straw hat who smells so strongly of mildew, you know he’s around even before you actually see him? Well, I like him. And I haven’t seen him in months. And it’s really really cold out there.

As of a month or so ago, the rumor was that he was in the hospital with pneumonia. [He was walking with a limp for a long time, like his foot was hurting pretty badly, so I’m hoping that, if he is in the hospital, it’s getting treated.] Then again, there are a lot of rumors, and variations of those rumors, about HG. To start, he’s supposedly wealthy [at most] – or at least didn’t become homeless for lack of cash. Some people say that his family sends monthly checks to a local storefront, which he picks up and spends. I’ve also heard that he has a sister that drops off money, but that there’s no crazy wealth to speak of. It’s clear that there’s some truth to him having at least a little stash: he does always buy his own Starbucks. Either he doesn’t need our money or he doesn’t want it – he won’t take your crumpled wads of cash on the street. I heard one person say they’d seen him actually chase people down to return their contributions.

Word on the street is that he’s a product of a tragic auto accident that killed his wife, leaving him lonely enough to go at least marginally insane. I feel like he wears a wedding ring, but I haven’t seen him in so long that I can’t remember. Either way, he definitely talks to himself in a high-pitched voice that reminds me of baby babble.

But, intentionally or not, he’s not totally disconnected from the rest of the world.

There’s definitely something to him. He’s a nice guy. For months and months, we passed each other on the streets or stood in line together at the Buckery [read: Starbucks] – and he finally started making eye contact with me. He leaves the baristas little presents in the form of tiny toy dinosaurs and snakes he hides in between the counter displays. My baby was always interested in the hat. He decorated it for the 4th of July.

Seems like everyone seems to look after Homeless Guy in their own way, passing on tidbits of information and worrying about his health when he’s looking rough. So where is he? And how’s he doing? If you know, share your intel!

[@CH3STNUTHILLER gotta love the hill: on daily starbucks run, ran into friendly neighborhood lawyer, sam rossitto, who just did our will http://bit.ly/c67Oy9%5D

A few years ago, while living in the DC area, my bff and I had a yard sale – and the owner of the neighborhood frozen custard store [that the Obamas visited!] stopped in and bought 2 graduation-themed picture frames from me. And all we could think was, “Oh my god! The Dairy Godmother herself was on our lawn!” She’s like a local celebrity. Seriously – during the holidays, when it’s her turn to stand outside her shop ringing the Slavation Army bell – EVERYONE walks by on purpose and gives paper, not change, to get on her good side.

That kind of thing happens every day in Chestnut Hill. I always see yoga lady Bobbi Tighe and her cute boyfriend chatting over coffee at the Starbucks, music lady Katie Drake running errands on the Avenue, you get the point.

Well, today, I ran into the guy who did our wills just last week. Do you know him? He’s Sam Rossitto. It was so weird to see him outside of the office – trading in his suit and tie for a trench, scarf and hat! He’s a thoughtful kind of quiet, until you get a few minutes into your appointment – then he’s a thoughtful kind of enthusiastic. He had answers to all of our [insane] questions. And he shared really well-balanced information about the scary stuff you have to think of when writing a document for your loved ones to follow, should you [at best] accidentally go all vegetable.

Honestly, we’d started working on our wills before, filling out paperwork we’d received from other attorneys back in DC. We’re not idiots – but it was complicated and a lot to think about on our own. It was easy to put off answering tough questions with a giant TV wooing us from across the living room. Sitting down with Sam took an hour on a Wednesday morning. He was super nice, really professional, obviously competant, and he made the process EASY.

So have you had a will drawn up? Didn’t think so. You know it’s important – so just do it. Give Sam a call. Or bump into him on Germantown Avenue – he’s the friendly-looking Chestnut Hiller wearing glasses and a cute fedora.